Sodium Carbonate → 8-(5-Methoxy-2-benzimidazolyl)sulfinylmethyl-1-methyl-1,2,3,4-tetrahydroquinoline

HRID 1088815Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1088815
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]2[N:7]=[C:8]([S:10][CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[C:16]4[C:21]=3[N:20]([CH3:22])[CH2:19][CH2:18][CH2:17]4)[NH:9][C:5]=2[CH:4]=1.ClC1C=CC=C(C(OO)=[O:33])C=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]2[N:7]=[C:8]([S:10]([CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[C:16]4[C:21]=3[N:20]([CH3:22])[CH2:19][CH2:18][CH2:17]4)=[O:33])[NH:9][C:5]=2[CH:4]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 150533328-(5-Methoxy-2-benzimidazolyl)thiomethyl-1-methyl-1,2,3,4-tetrahydroquinoline

Produkt 1

HCID 150533118-(5-Methoxy-2-benzimidazolyl)sulfinylmethyl-1-methyl-1,2,3,4-tetrahydroquinolineAusbeute 45,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 8-(5-methoxy-2-benzimidazolyl)thiomethyl-1-methyl-1,2,3,4-tetrahydroquinoline (0.80 g) in dichloromethane (30 ml) was added a solution of m-chloroperbenzoic acid (80%, 0.51 g) in dichloromethane (10 ml) by use of a pipet at -60° C. The mixture was stirred for 30 minutes at the same temperature. Aqueous sodium carbonate was added to the reaction mixture and the mixture was extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate and the solvent was distilled off. The resulting residue was purified by silica gel column chromatography [eluent:ethyl acetate-n-hexane (2:3)] and recrystallized from ethyl acetate to give 8-(5-methoxy-2-benzimidazolyl)sulfinylmethyl-1-methyl-1,2,3,4-tetrahydroquinoline (0.38 g).

Aufarbeitung

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off
  4. customThe resulting residue was purified by silica gel column chromatography [eluent:ethyl acetate-n-hexane (2:3)]
  5. customrecrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-d9b986387d474111be66cccba7e251e4
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04963566

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